The Many Problems of Sam Winchester
by trenchcoatsexual
Summary: "The problem with Sam Winchester's life is that there are so many problems and each and every one of those dilemmas can somehow be traced back to, referred to, originated from, or be directly related to his best friend: Gabriel Novak." High school AU


**Words: **9,546

**A/N: **So this started out really short then took on a life of its own. Apparently, when I'm stuck with writer's block, I write Sabriel. :S Hope you like it, I'm kind of proud of this one. :D

Thanks again to my beta/girlfriend for her support. Seriously. I can't do shit without her. I'm hopeless.

* * *

The problem with Sam Winchester's life is that there are so many problems and each and every one of those dilemmas can somehow be traced back to, referred to, originated from, or be directly related to his best friend: Gabriel Novak.

* * *

The problem with Gabriel Novak is…well, that he's Gabriel Novak. It's just his basic, all around personality. He's addicted to candy, yet doesn't gain any weight and Sam has no idea how the hell he manages it because Gabriel has got to be the laziest person he's ever met. He makes the crudest, lamest jokes known to humankind. He's obnoxious and loud and boisterous where Sam is reserved, quiet, controlled. But for some reason, they work.

Gabriel is a little older than Sam. And 'a little older' means that Sam is a senior in high school and Gabriel is a senior in college. It's never affected their relationship much, especially since Gabriel acts more like the child of the duo. He and Sam met when the Novaks- all eight of them- moved into the house down the street from the Winchester's.

Sam had been four years old, playing in the neighborhood park. He was building a castle in the sandbox when ten year old Azazel came around and kicked it down, stomping it into the ground. Sam's eyes had filled with tears as Azazel laughed, and then a high-pitched voice came from behind them and they both turned to look.

"Big, bad dragon Azzy destroying little princess' castles, huh?" Gabriel, a few weeks from his ninth birthday, leaned against the swing set, a lollipop in his mouth.

Sam was about to protest, because he was _not _a girl, but Azazel got there first. "Would that make you the knight in shining armor?" he taunted, a sneer that was much too wicked for a ten year old on his lips.

Gabriel pulled out the candy from his mouth and smirked. "Someone's gotta kill the evil dragon, right?"

Something passed between the two boys, something Sam supposed was a big boy thing, because they just looked at each other menacingly for a minute, and then Azazel stomped off. Gabriel looked extremely pleased with himself as he stepped into the sandbox with Sam.

"You okay, princess?"

Sam glared up at him. "I'm _not _a girl!" he snapped.

Gabriel raised his hands in defense before he reached into his back pocket and took out another lollipop, offering it to the little boy who was trying to inconspicuously wipe his eyes. "Here."

Sam eyed the candy warily. "Momma says I'm not supposed to take candy from strangers."

"Not even strangers who just saved your little princess butt from the evil dragon?" Gabriel challenged playfully. "My name's Gabriel. I moved in last week. What's your name?"

"…Sam," the younger boy answered slowly.

"Well, Sammy, now we're not strangers. So it's okay if you take my candy."

There was no way Sam could argue with that logic- and the lollipop was cherry-flavored, which was his absolute favorite _ever_- so he took the candy and unwrapped it, sticking it in his mouth. Gabriel smiled widely around his own sucker and sat down in the sand next to Sam. "Let's see if we can save your castle, Princess Sam."

"'M no' a p-inthess," Sam grumbled around the candy, and Gabriel just grinned wider.

"You've got the hair for it." He batted at the ends of Sam's long hair playfully and Sam jerked away indignantly, but didn't push Gabriel away when he started rebuilding the destroyed castle.

By the time Dean came back from playing baseball with his friends to pick him up and walk him back home, Sam had a miniature five story citadel with a moat and alligators surrounding it, a flag made from a twig and the lollipop wrapper on the highest tower, and a large clock that would put Big Ben to shame.

Sam waved at Gabriel as Dean led him away.

They'd been best friends ever since, and that was cool.

Sam's dilemma was that when he turned fourteen, he realized that he was in love with the dick he called his best friend. Goddamned Gabriel Novak.

* * *

The problem with Castiel Novak is that he's extremely observant.

Many people at school think that Cas is stupid because he's shy and has a tendency to stare at mundane objects such as potted plants with an expression of utter bewilderment, like he has no idea what its purpose could possibly be. But Sam knows different. Sam knows how brilliant Cas is.

The two met when Sam and Gabriel were playing together as kids. Gabriel invited Sam over for cookies at his place, and that's where Sam found the little blue-eyed boy that was his age sitting at a kitchen table that was much too tall for him, munching on a chocolate chip cookie. When school started, Castiel and Sam found they were in the same kindergarten class and decided to stay close together because even though they didn't know each other well, it was better than being with complete strangers.

They shared lunches and slept next to each other at nap time. In third grade, they learned that Cas was really good at math and Sam wasn't and that Sam was really good at English, which Cas wasn't. They started doing each other's homework and still shared lunches, but they didn't sleep together anymore because- _awkward. _Sam often slept over at the Novak house, however, and hung out with both Gabriel and Castiel.

It was through Sam that Dean and Castiel met, and the two became the best of friends. They did everything together, just like Gabriel and Sam.

Back to the point- Castiel is not stupid. He's unique, and extremely intuitive. Sam often feels like he's being X-rayed when Cas fixes that electric blue gaze on him and studies him, like he's seeing Sam's very insides.

One day, completely out of the blue, Cas turned one of those looks on Sam and appraised him for what felt like a full minute before he finally spoke.

"You're in love with Gabriel, aren't you?"

Sam choked on the Coke he had been drinking and Castiel impassively tapped him on the back. Once Sam had regained his composure, he looked at his friend like he'd lost his mind.

"Dude!" he exclaimed. "What the hell? Why do you think that?"

Castiel gave him another considering look that lasted so long that Sam felt like he was about to slap him. Just before he snapped, however, Castiel shrugged nonchalantly and turned back to the television. "No reason," he responded calmly.

Gabriel came back from the kitchen in that moment, brandishing a brand new bowl of popcorn, a full on grin on his face from the prospect of food. Sam instinctively straightened up and his lips twitched into a smile at the sight. But not at the sight of the popcorn, at the sight of _Gabriel. _Who the hell got butterflies in their stomach from being handed a bowl of popcorn? Well…Gabriel probably did. But Gabriel was addicted to all kinds of food- except the green ones. The look of pure joy on his face when he ate candy was something to warm anyone's heart, and his laugh made stomachs flutter all over the place, especially if they were the cause of that laugh and-

Sam stopped himself and glanced over at Castiel, who was resolutely looking at the television, pretending he hadn't noticed anything at all. But if that slight knowing tilt to Castiel's lips was anything to go by, Sam was sure Cas had just seen how he had reacted when Gabriel walked into the room and much more than that.

Castiel, Sam decided, wasn't the one with the problem. Or, technically, he wasn't the cause of one of Sam's many problems, as Sam had originally thought. Because it was Sam who made it more obvious than daylight how he felt about Gabriel. Castiel just woke up earlier than most people to see the blinding rays of Sam's complete and embarrassing adoration filter in through the drapes of his denial and insecurity.

Okay. Crossing off 'poet' from the list of potential future professions.

* * *

The problem with Dean Winchester is that he always gets what he wants, and he doesn't even try.

Right now, Dean is a junior in college. Or- he's supposed to be. But he dropped out halfway through his second year. He decided it just wasn't for him. Instead he works at their Uncle Bobby's garage, and makes more money than he would have had he been paying for school and books and crap just to end up at the same job. Everyone decided that it had been the right decision, even though their mother had been heartbroken at first, thinking that her son had given up on himself.

But Dean was doing great. He had a steady paying job and he was happy and carefree. He made people laugh and he took care of everyone and that's what he wanted. Which brings us back to 'he always gets what he wants'.

For example (or, really, the greatest example of all), Castiel.

Sam had first brought Castiel over to his house one day after kindergarten when they learned that they shared a passion for dinosaurs. Sam wanted to show Cas his dinosaur collection. He had been afraid that Dean would pick on Cas because he was so different. But that hadn't been the case at all.

After Sam introduced them, Dean had made a comment about Cas' 'freaky blue eyes'.

"They're just like Professor Xavier's!" Dean had said jovially. "Can you read minds?"

Sam had thought his brother had hurt his new friend's feelings and tried to usher him away and apologize, but Castiel wouldn't budge.

"I do not understand," he said, voice small and confused. "Who is Professor Xavier?"

Dean crossed his arms in irritation. "Professor X, dummy! From the X-Men."

Cas quirked his head, frowning. "What are X-Men?"

Dean's eyes bulged out of his head. "You-You d-don't….you don't _know_…."

Sam had managed to pull Cas away, leaving his brother to splutter and flounder as he and his new friend talked about dinosaurs in Sam's room. Castiel liked pterodactyls because they could fly. Sam's favorite was the brontosaurus because it was really, really big but really, really gentle.

The next morning before they left for school, Dean asked Sam to bring Castiel over that afternoon too.

When Sam and Castiel arrived, Dean grabbed the nervous-looking blue-eyed boy by the wrist and dragged him upstairs, where a large stack of comic books sat, waiting to be explained and dissected. The door slammed shut and Sam understood that he was not invited. So he shrugged and went down the street to play Mario Kart with Gabriel.

After comic books, it was cartoons, then TV sitcoms and action movies. Dean had found someone other than Sammy to take care of and teach new things and Castiel found someone to pay him their undivided attention after coming from a family of six children. They became practically attached at the hip.

Sam's first clue about Dean's crush was the way they'd look at each other- when they knew the other wasn't looking. He thought it was normal behavior for Cas, since he was always staring strangely at people. But it was definitely odd for Dean, who reserved his emotional, meaningful looks for pies and his car.

The second clue was how Dean kept turning down dates with the hottest girls in school in favor of hanging out with Cas. Jo Harvelle, Anna Milton, Cassie Robinson. And then there was Lisa Braeden.

Lisa, Dean's on-again-off-again girlfriend, became his permanent ex in Dean's senior year when Sam and Cas started high school. (Another minor clue to note: Dean managed to score the locker next to Castiel's somehow. Sam was sure he had threatened the original owner with physical violence.)

Sam's third clue was a little more obvious. And by 'obvious', he means walking in on his brother and best friend half-naked, Dean kneeling on the floor between Cas' spread thighs. The less Sam says about the look of utter bliss on his friend's face, the less therapy he'll need.

Neither boy noticed him, so Sam shut the door quietly and sulked off to his room.

It wasn't fair that Dean had gotten his Novak before Sam had gotten his.

* * *

The problem with Jessica Moore was that she was perfect.

She was everything Sam needed- she was pretty, smart, headstrong, independent. Jess was flawless.

They started dating when Sam was fifteen and well aware of his burgeoning crush on his best friend. Sam decided to leave the subject untouched by himself and everyone else, an ugly, blistering feeling at the back of his mind. Jess deserved better than a person who tried to use her to get over someone else.

Unfortunately, it didn't matter either way because Jessica moved away again five months after they started dating.

No one was more beat up about the break up than Gabriel was.

The day after Jessica moved away, Gabriel came over to the Winchester house with a wagon-load of candy and video games. And, no, that's not an exaggeration.

When Mary Winchester opened the door to find Gabriel Novak grinning at her, hauling an old-fashioned red kiddie wagon like the ones in the cartoons, she didn't even blink. Not even when she noticed the mountain of colorful candies and treats piled high.

"Hiya, Mary!" Gabriel greeted cheerily.

"Hi, Gabe," she replied with exasperated fondness. "Come in. Sam's watching TV in the living room." She stood aside and held the door open so he could drag the wagon inside. "Try not to scuff the floor, please."

"Yes, ma'am," he said, giving her a salute with his free hand and leaning in to peck her cheek as he passed by her.

Mary shoved his shoulder playfully. "Don't call me ma'am, Gabriel. You know that makes me feel old."

"Well, Mary, they say women age like fine wine. If you keep getting any older and any more beautiful, I'm going to have a serious problem with your husband." He waggled his eyebrows suggestively and she rolled her eyes, too used to it to be appalled.

"Stop hitting on my wife, Novak," came John Winchester's gruff tone from the kitchen, too used to it to be angry.

"Yes, sir!" Gabriel called back, grinning impishly as Mary giggled.

She followed him to the living room, where Sam was slouching on the couch in sweats, long legs propped up on the coffee table, the History channel droning boringly from the TV. He's not surprised when he sees Gabriel, having heard his father admonishing him. But when he sees the wagon of candy, he looks at his friend in annoyance.

"Aw, dude! What the hell is that?"

Before Mary could chastise her son for language, Gabriel was launching himself onto Sam with an exaggerated cry of, "Sammich!"

Sam gasped as Gabriel collided with his chest and didn't resist when Gabriel adjusted them both on the couch so he could pull Sam's head down and press it to his chest, tucking it under his chin and stroking his hair as if Sam were a small child. After years of friendship, Sam has learned it's easier to let Gabriel have his way than struggling.

"My poor boy!" Gabriel wailed like an actress in a bad telenovela. "My poor, sweet Samsquatch!"

Mary rolled her eyes fondly at the boys and left to the kitchen.

"Gabe, come on," Sam grumbled, trying to pull out of his friend's grip. "Let go, you dick."

Sam managed to wrench himself free and Gabriel buried his face in his hands and let out a large, fake sob. "I'm sorry," he wept, voice muffled by his palms. "It's just that I was hoping you would finally get laid." He wiped away an invisible tear and said in a high-pitched voice, "All my hopes and dreams are _crushed._"

Sam huffed and settled back into the couch, picking up the remote and flipping through the channels for one Gabriel would enjoy more. "Go home, Gabriel," he groused, settling for a really bad reality show that Gabriel liked for some reason.

The older boy didn't go home, obviously. Instead, he pulled out a Snickers bar for himself and a packet of Gummi bears for Sam from his stock pile. They munched as they watched some drunken slut fall, her skirt doing nothing to hide what the censor blur did.

After a while of easy silence, during a commercial break, Gabriel nudged Sam's arm with his elbow and turned to look at him. "Hey," he said softly. "I really am sorry about Jess, kiddo. I know how crazy you were about her."

Sam chewed on a Gummi bear and looked at Gabriel. The sun was low and filtering in gold through the windows behind him, so his hair looked ten shades lighter than normal and almost glowing, like a halo. The slight shadows and the small smile on his lips made him look soft and warm, like the breeze on a summer day, taking Sam's breath away.

"Y-Yeah," he croaked, swallowing the Gummi bear. It went down like a rock through a rusty garbage disposal. "Me too."

Gabriel gave him a sympathetic look then turned back to the TV. "I mean...compared to all the other chicks that took an interest in you..." Sam winced. "Madison was okay, but she gave a whole new definition to the term 'PMS'. It was like the friggin' Hulk once a month, y'know...eesh. Then psycho stalker Becky...and the less said about _Ruby,_ the better." They both visibly shuddered at the memory. "Compared to them...Jess was a friggin' angel."

Sam didn't comment, and they fell into another silence, until Gabriel broke it again. This time with a much more agreeable comment.

"Wanna play some Halo? Get your mind off it?"

"Sure," Sam grinned. He'd probably agree to anything his friend suggested, just as long as he kept sitting so close to him, the warmth seeping through their shirts and into their skins, Gabriel's ever-present chocolaty scent filling Sam's nose. Just as long as Gabriel kept turning those golden eyes, sparkling with mischief, on him, smiling at him like they always did.

With one of those big, bright smiles that Sam loved so much, Gabriel turned to his wagon and pulled out a video game case and got off the couch to the TV to set up the X-Box. If Sam unabashedly stared at the way Gabriel's pants rode down as he crouched, exposing the waistband of his boxers, no one was around to call him out on it.

They played for three hours, Gabriel eating most of his arsenal as he kicked Sam's ass, using his sugar rush to his advantage. They bickered and bantered and shoved each other's shoulders, laughing the whole time.

As they were entering their fourth hour of Halo 3, Gabriel crashed as he usually did after a sugar rush. His head landed on Sam's shoulder, snoring lightly, and Sam grinned, turning off the X-Box and turning the TV back on without moving from his position. He propped his legs back up on the coffee table and leaned back on the couch, letting Gabriel lean most of his weight against his side, drooling slightly on his shoulder.

If this is how he was going to be consoled, Sam thought, maybe he should have girlfriends move away more often. Maybe Jess hadn't been a problem at all.

* * *

The problem with Sam's basketball games is that Gabriel meets Kali at one of them.

Sam first got into basketball as a freshman, when he had his growth spurt. Gabriel, a senior at that point, was walking with Sam and they saw a poster announcing the basketball team tryouts. Up until then, Sam had been short and scrawny, but that summer he had grown three inches, his limbs shooting out and his ribs threatening to break his skin. Gabriel had been teasing him about it and Sam had shot back that he was just miffed that Sam was catching up to him (which he did, then surpassed, three months later).

Upon seeing the poster, Gabriel had beamed, saying, "Hey, look, Sammich! Someplace where your ridiculous height will be useful! Y'know, once you gain just a few more inches, of course."

Sam had made a face and shoved his shoulder lightly. "I don't play basketball," he replied, as if that settled the point and they could move on. But Gabriel wouldn't let it go.

"No, seriously, kiddo. I say you give it a shot. Maybe shoot hoops with Dean to see if you like it. You've never even tried it."

"Why can't I shoot hoops with you?" Sam asked, cocking his head. Gabriel raised a sardonic eyebrow at him and Sam remembered- physical exertion and Gabriel go together like peanut butter and dirt. Although Gabriel would probably still eat it, just because it had peanut butter.

That afternoon, Sam asked Dean to play some basketball together to see if he liked it. _Not_ because Gabriel had suggested it, of course. Just because Sam was curious.

As it turns out, Sam did like it, and he tried out. He got the very prestigious position of Benchwarmer #1 for the first three games, and Gabriel came to each one. He'd never been to a school game in his life, but he promised Sam that only death and the sudden appearance of Adriana Lima naked in his bed would stop him from coming to one of his games. Even if Sam did nothing but examine his own nails for the first ones.

The fourth game into the season, Sam finally got to play. He did well. It wasn't a dramatic debut by any means. He didn't score the final point at the buzzer or slam dunk three in a row. He did, however, make some fantastic passes and danced around his opponents gracefully. He even scored a point and got applause for it. No one louder than Gabriel's (he even had a bullhorn, calling out 'Winchester! Winchester!' through it and making Sam blush). Not even Mary or a beaming Dean could compete with the ruckus Gabriel was making.

At the end of the game, Gabriel, Cas, and his family came up to hug and congratulate Sam. Gabriel pulled Sam into a headlock and ruffled his hair, exclaiming, "That was some fancy footwork out there, Princess!"

Sam's breath caught the same way it always did when Gabriel called him that. He didn't do it often, only during really special occasions. Anyone who overheard would think that Gabriel was simply teasing Sam for his girlish moves on the court, but they both knew better.

Ever since that first day they'd met, 'Princess' was a name Gabriel used as the greatest term of endearment towards Sam, and he didn't call anyone else that. With just that name, Sam knew how incredibly proud and happy his best friend was towards him and just the thought made Sam's heart flutter, lighter than he'd ever felt before.

Gabriel didn't call Sam that after every game, of course. Then it would lose what made it special. But that one time, that first time, Sam held on to for every game. It's what made him play better, practice harder, be the best he could be so that every time he scored, Gabriel would look at him that same way.

Sam stayed on the basketball team through all four years of high school. It was in his senior year that Kali moved into town. She was a year older than Sam, but since she couldn't finish her last year at her old school, for whatever reason (Sam had his money on being a serial murderer who changed her name and fled the state, but Gabriel always ignored him), she had to take her senior year all over again.

It was during one of the school games in Sam's senior year- the only time Gabriel ever came to the school anymore since he was in college now- that Sam looked up into the stands to wave at him, since he was on the bench for the first half. Sam was team captain now, and the strongest player they had. So they saved him for last.

He'd found Gabriel, but he wasn't looking down at the game. Instead, he was talking to dark-skinned, heavy-lidded, pretty-lipped Kali Masterson. Gabriel was talking, like usual, and Kali was smirking at him, red lips curling slightly at the corners, pretending to be interested in what he was saying. She twirled one of her long dark locks around a finger whose nail perfectly matched the shade of lipstick she wore.

Gabriel finished whatever he was saying and Kali responded eagerly with some comment of her own, laying her other hand gently on his arm. Gabriel looked down at it briefly with a grin, eyes flashing up to her face again, pausing at her lips before meeting her eyes as she continued talking.

A fireball started roiling in Sam's stomach and his breath came heavy, fists clenching.

When it was his turn to play, he simply couldn't focus. He was so angry, vision blurring with it, that he knocked Gordon Walker straight on his ass, not even noticing it until the referee was blowing his whistle, calling a foul.

That got both Sam's and Gabriel's attention. Sam snapped out of his angry haze and held out his hand to Gordon, apologizing profusely. Gordon, having always been a dick to Sam, sneered at him and ignored his hand, getting up to take his foul shot. As Sam stood on the line, he looked up at Gabriel, who was looking back at him, a concerned expression in his eyes.

Sam just watched, anger mounting again, as Kali tried to regain Gabriel's attention, touching his face with one perfectly red, manicured finger to turn it back towards her. He got back into their conversation, but his eyes kept flashing to Sam, and Sam tried to keep from feeling a little bit satisfied that he had at least half his attention.

Gabriel's worried glances kept Sam focused enough that he didn't lash out again during the game, but they lost anyways. As the other team cheered and celebrated, Sam sulked over to the bench to grab his bottle of water and his bag. He caught sight of Kali writing something- most likely her number- on Gabriel's arm before she kissed his cheek and walked away.

Sam rushed out of the gym before Gabriel could find him, big red lipstick stain on his cheek.

As Sam walked back home with hurried, furious steps, his heart thudding like a rabbit's, he wondered if Kali would be another problem. It wasn't the first time Gabriel had dated, of course, but something felt different about this. He didn't know much about Kali, but she seemed dangerous. Not someone who would let go of something she set her eyes on. Sam had the sinking feeling that maybe Kali would be his biggest problem of all.

* * *

The problem with Gabriel's brain-to-mouth filter was that it didn't exist. What Gabriel wanted to say, Gabriel said, not caring who heard.

Fortunately, he had _some _restraint around Sam's parents. Not much, but enough.

John and Mary were getting ready for dinner with Bobby and his new girlfriend Jodi. It was apparently a fancy affair, since Mary was wearing a sleek black dress with her best pearls, her blonde curls done up, a few falling to frame her sweet face.

Gabriel was sitting at the kitchen table with Sam, eating some sandwiches they had prepared when Mary came downstairs, heels clicking on the linoleum, looking for her wallet. Gabriel's jaw dropped, eyes bugging out of his skull. Sam kicked him in the shin under the table.

"Quit perving on my mom, Gabe," Sam grumbled around a bite of sandwich and Mary looked at them both at the comment, another fondly exasperated look on her face. Those were so common as to almost be permanent whenever Gabriel was around.

"Shut up, Sam," Gabriel shot back, glaring at his friend before turning his most charming smile towards Mary. "Why, Mary, you truly are a vision of beauty. How do you do it, surrounded by nothing but disgusting, graceless men all day?"

As if on cue, Dean came out of the living room, hair flattened down on one side from his nap on the couch, wearing nothing but a white undershirt and a pair of boxers. He yawned, scratching his chest, opened the fridge and dug around for a beer. When he passed by Mary to go up the stairs, he kissed her cheek and muttered, "Lookin' good, Ma." His eyes weren't even open all the way.

All three of them stared after him, mildly disturbed.

"I rest my case," Gabriel said.

John came down the stairs in his smartest suit, tie undone, hair slicked back and smelling of crisp cologne. Gabriel let out a low whistle. "You clean up _nice, _John," he admired.

Sam rolled his eyes and kicked him again, still focused on his sandwich. "Quit perving on my dad, too. Jeez."

John raised his eyebrow as Mary did up his tie. "Was he hitting on Mary again?"

Gabriel grinned. "Could you blame me if I was, John? Besides, I wasn't exactly hitting on her. I was just telling her how I would gladly sweep her off her feet and away from this testosterone-filled hole. Take her away somewhere her beauty will be appreciated and worshipped every day."

As John came around the kitchen table to get his keys, he cuffed Gabriel on the back of the head. "Try it and you'll be dead before you hit the ground."

Mary rolled her eyes with a smile. "John, leave the boy alone. He's just being a kiss-ass."

Sam snorted and Gabriel laughed.

"Besides," Mary continued, checking her hair in her compact mirror, "Gabriel's already got a lucky lady to appreciate and worship, don't you?" She turned her smile on Gabriel and Sam resisted the urge to groan and mope.

"That's right, I do," Gabriel grinned. "But you'll always be my number one lady, Mary. No need to be jealous."

There was a collective eyeroll around the kitchen.

"So how _is _Kali?" Mary asked him, leaning against the table with a smile.

Gabriel swallowed his bite of sandwich before answering. "She's great. Thinking of applying to Princeton. Whoever said Gabriel Novak couldn't score a smart, beautiful chick is an idiot." Sam didn't think Gabriel's voice could get any smugger than usual. Apparently, he was wrong.

That's what Sam hated the most. How _proud _of Kali he was. How he _bragged _about her to everyone who would listen. Because that's the kind of guy who Gabriel was. The kind that bragged about the people important to him. He used to brag about Sam that way. About Sam's grades, his smarts, his talent on the basketball court, his kindness. Now it's all about _Kali._

"How long have you two been together now?" Mary asked curiously.

"Three months," Gabriel replied easily, because he was also the kind of guy to remember things like that. Anniversaries and all that other useless crap that most guys didn't give a crap about- Gabriel thought they mattered. Because if it mattered to someone that mattered to him, it mattered to him too. Sam resisted the urge to sigh wearily.

"Mary, come on, we're gonna be late," John said after checking his watch.

Mary came around the table to kiss both boys on the cheek. "You two take care now. We'll be home late, so don't wait up."

"'Kay, Mom," Sam smiled. As she left the kitchen, he called her back. "Hey, Mom! Gabriel wouldn't let me get in a word in earlier, but you really do look great."

Mary beamed at him and tossed him another kiss before hurrying out the front door after her husband.

"You wanna know what the best thing about Kali is? Besides being smarter than the average Einstein and beautiful as all get out?" Gabriel asked rhetorically after they'd finished off their sandwiches. "She gives _great _head." He waggled an eyebrow at Sam and nudged his ribs and Sam fought off the urge to puke.

Yeah, Kali was a big problem in Sam's life for all that Sam saw her a total of five times a day walking down the hall. Maybe if Gabriel didn't talk about her all the time, say things like _that_, maybe it wouldn't be such a big deal.

* * *

The problem with Sam's internet history was that it was easily accessible to people like Dean who didn't have computers of their own and needed their little brother's to Google something stupid. Like, 'How long can a sex-addict go without sex?'

Sam had found that particular search on his computer after Dean and Cas had some sort of lover's spat.

In the case that it becomes troublesome for Sam, Dean was looking for something actually useful. 'What kind of oil is better for a '72 Mustang convertible?' At least it was for work.

Unfortunately, Dean somehow managed to stumble across Sam's internet search history. The history included various gay porn videos, advice websites with tips on how to give a better blowjob or how to be a better lover.

Sam came in to his room as Dean was scrolling through the list and when he got a closer look at what Dean was looking at, he turned a beet red, screeched, "Dude!" and slammed the laptop shut, narrowly missing Dean's fingers. "What the hell?"

His brother turned to him with a raised eyebrow. "You know, that last link looked pretty useful."

Sam's nostrils flared and his fists clenched, feeling just about ready to lash out at Dean. "Get out of my room," he hissed.

Dean rolled his eyes. "All that stuff- that's for Gabe, isn't it?"

Sam's heart sank to his shoes, face draining of all color. "Dammit…Cas told you, didn't he?"

"He told me his suspicions," Dean shrugged, leaning back in Sam's desk chair. "But I had already figured it out before he told me."

"Am I _that _obvious?" Sam groaned, sitting heavily on the bed and burying his face in his hands.

"To the people that know you, yeah." Dean nudged Sam's leg with the toe of his boot. "How long have you two been doing this? Is that Kali chick like his beard or something?"

Sam looked up at him with a frown. "Gabe and I aren't doing anything."

Dean looked confused for a moment and opened his mouth to ask, but his face cleared as it clicked. "Aahhh…but you _want _to. And Gabe doesn't know."

"Shuddup," Sam groused, flopping back on the bed and staring up at the ceiling.

"You should tell him, bro," Dean suggested wisely.

"But Kali-"

"He's known you longer," Dean cut in. "You're more important to him."

And maybe Sam's biggest problem was that his stupid older brother was sometimes right, but Sam just refused to see it.

* * *

The problem with Sam's anger was that it often got the better of him. It made him say things without thinking, made him lash out at people he wanted to keep closer.

But, really, it wasn't Sam's fault he snapped. Not when Gabriel dropped a bombshell like _that _on him.

"What the hell do you mean you're going to ask Kali to move in with you?"

Yeah, okay. Maybe he was overreacting a little bit. Because it hadn't been a _bombshell_ exactly. In fact, it had been more of a gust of wind, hitting him in the face momentarily and ruffling his hair a little. But to Sam, it felt like a brick wall slamming into his nose.

"I didn't say I was _going _to!" Gabriel shot back, shocked at his friend's sudden outburst. And he really hadn't. He had said he was _considering _it. He had mentioned it lightly, in passing, a fleeting comment.

Ever since his second year of college, Gabriel had been living in his own little apartment closer to the campus, but still pretty close to their neighborhood. At first, Sam had been worried that they wouldn't see as much of each other because of it, but Gabriel spent most of his free time at the Winchester home anyways. And Sam had found himself visiting and staying over at Gabriel's apartment often enough. Just as he had been doing when Gabriel dropped the bombshell/gust of wind on him.

"You've only been together six months, Gabriel!" Sam practically shouted, shooting to his feet.

"I know!" Gabriel snapped. "But her parents are really strict and they're kicking her out after graduation and she's got nowhere to stay!"

"She can go stay at Princeton, then!" Sam spat.

"She can't!" Gabriel shouted, getting to his feet too. "Not until fall semester starts! It's just for the summer till she can move out there!"

Sam breathed in hard through his nose. He wasn't naïve and he saw no point in fooling himself. There was no point in thinking that he was the only one who visited Gabriel's apartment. He'd seen Kali's things lying around often enough to know she had at least spent the night. There was no point in thinking that he was special to Gabriel.

Gabriel's apartment only had the one bedroom and the couch wasn't pull-out, not that he or Kali would use it even if it was. Sam knew how fast Gabriel moved and he could only guess that Kali was just a step behind him the whole way. Gabriel had bragged about his sex life often enough for Sam to know.

But spending one night having sex and _living _together were completely different. The implications behind living together were staggering, daunting. Sam had been hoping all this time that Kali would be just one of Gabriel's fleeting flings. But _moving in together_- that was serious.

"Why are you acting like I shaved your head about this?" Gabriel asked him grimly, and Sam could see he was pretty upset by Sam's reactions.

Sam looked away. "I just don't like Kali, okay?" he muttered darkly.

"Why not?" Gabriel didn't sound angry, just curious, but his face betrayed the hurt he felt. "She's my girlfriend."

Sam looked back at Gabriel, chest heaving angrily. He thought about that statement. 'She's my girlfriend.' And Sam found himself wondering, for the millionth time since the couple had gotten together, _why_?

Why was Kali Gabriel's girlfriend? Was is because the sex was good? What _the hell _did they have in common? What _the hell _did she know about Gabriel?

Did Kali know that for all of Gabriel's infamous sweet tooth, he _hated _Raisinets? Did she know that Gabriel had learned all his pranking tricks from his older brother Luke? Did she know that Gabriel had even gotten one over on Luke and earned himself the title of Trickster in the Novak house? Did Kali know that all the Novak children were named after angels and Gabriel _hated _that because he didn't have a religious bone in his body?

Did Kali know that Gabriel hated his stepmother? Did she know that Gabriel still had nightmares about the housefire his mother had died in? And if she knew, it was because Gabriel had told her, not because she had been woken up in the middle of the night during a sleepover by Gabriel's crying and comforted him until they fell asleep together like Sam had done. Seven times. In three years.

If she knew, it was because Gabriel had told her and not because he had called her in the middle of the night, asking her to _just talk to him _until he calmed down and fell asleep with the phone pressed to his face. Because Gabriel called _Sam. _Because Gabriel- independent, funny, carefree- still called Sam crying.

Sam knew Gabriel better than anyone. He knew every side to Gabriel. He had seen how Gabriel transition from friend to student to son to brother. Sam knew each one of his faults and each one of his strengths, every good and bad thing about Gabriel. And Sam loved him despite and because of them all.

The only thing Sam didn't know about Gabriel was what Kali knew and what Sam wanted to know more than anything else- what Gabriel was like as a lover.

Who gave her the right to take that from Sam? She was no one. Compared to Sam, she was _no one _and she was stepping into his territory uninvited.

"That's _why _I don't like her, jackass," Sam said, throwing all caution to the wind. "_Because _she's your girlfriend."

Gabriel stared at him as if he'd grown a second head. "W-What?"

Sam groaned, irritated. "I'm _in love _with you, Gabriel," he elaborated, not really caring if Gabriel knew or not. It didn't matter anymore. He had chosen Kali. "I have been since…basically forever, I guess. So…just…forget it, okay? Do whatever you want with Kali. I don't really give a shit."

With that, Sam made his way towards the door, picking up his jacket on the way. Gabriel called his name, but Sam didn't turn back. He just wanted to leave, get _away _from Gabriel and his goddamn perfection and the way he had stolen Sam's heart so irreversibly.

As Sam turned the knob and opened the door, a hand flashes past his arm and slammed it shut again, then grabbed his arm and spun him around, pushing him up against the door in one swift movement.

Sam glared down at Gabriel's intense face. "Gabriel, I don't want to talk-"

Apparently, neither did Gabriel, because he pulled Sam down by the back of his neck and surged up to meet him for a hard kiss.

The first millisecond, Sam managed to think, _What the hell? _After that, he didn't think much and just _reacted, _because Gabriel was _kissing _him and that's all Sam had ever wanted.

Sam shoved his fingers into Gabriel's stupidly gorgeous hair and pulled him in harder for a deeper kiss. Their tongues met somewhere in the middle and Sam's teeth grazed Gabriel's bottom lip.

There was a wall somewhere behind Gabriel and Sam stepped forward until the shorter man was pressed up against it. Gabriel's hand found the back of Sam's head, tangling his fingers in the long, soft, floppy locks. His other hand gripped Sam's waist possessively.

They kissed and kissed for what felt like hours until their breaths were coming in so hard that it hurt their lungs and their lips were numb and swollen.

"What about Kali?" Sam whispered between pants, nose bumping Gabriel's.

"Who?" Gabriel slurred. Sam raised an eyebrow at him. "Oh! Her! Kali, right!" He then started peppering Sam's jaw with little kisses and Sam used to have coherent thoughts, really. At some point. Not anymore.

Sam made a little noise in the back of his throat and his knees started to give away a bit, so Gabriel moved them over to the couch. He sat Sam down and plopped down next to him, pulling him in for another kiss. Sam parted his lips willingly and snaked an arm around Gabriel's waist.

Gabriel's hand smoothed over Sam's chest, hardening and broadening after passing through puberty and rigorous workouts to stay in shape for basketball. Sometimes Gabriel thinks about how gorgeous Sam's body will be in a few years after toning up some more and his mouth waters, but no one needs to know that.

"Gabe," Sam whispers, pulling away from him slightly because he needs to regain control of his brain, dammit! "_What about Kali?_" he stresses, putting enough force behind his words that Gabriel understands he can't evade the topic again.

"I guess we're over then," Gabriel said, and he sounded as depressed about it as a kid being presented with chocolate cake.

Sam raised both eyebrows. "Just like that?" And yeah, Sam felt like a million bucks right now because Gabriel had chosen _him _over sex goddess Kali, but he still felt a little because he had essentially just stolen her boyfriend from her and it's not like she had done anything to him. Not _really_.

"I guess so, yeah," Gabriel replied, turning his eyes on him, looking like melted gold. There was a cocky smirk on his face, but Sam could see that there was something serious and intense behind those eyes. "I don't really want her if I can have _you_, Princess."

And that was it. That was as good an admission of love as Sam could ever ask for. Kali be damned, Gabriel was _his._

The next kiss was hungry and desperate, trying to get as much of the other as they could. They had known each other for, what? Fourteen years now? That was a lot of time to make up for.

Sam's hands pressed Gabriel's shoulders against the back of the couch and he moved, looming over the smaller man.

Small sounds escaped both their lips, just to be swallowed by the other. Sam trailed his mouth to the side, kissing across Gabriel's cheekbones and along his jaw, down his throat. His hands slipped down from Gabriel's shoulders to his hips as Gabriel's found his hair again.

Both their pants were straining at this point and Sam wanted to show Gabriel that he was worth choosing, that he could be as good and better for him than Kali. He wanted to prove to Gabriel that he had made the right choice.

Sam fell to his knees, hands spreading Gabriel's thighs, still kissing along his throat and collarbone. Once Gabriel's brain caught up enough for him to realize what Sam's intentions were, his hands flew up to Sam's shoulders, pushing him away gently.

"Woah, woah there, Sam!" he exclaimed, a slightly worried look on his face. "Slow your roll, kiddo. We can take our time. There's no rush-"

"Shut up," Sam interrupted irritably, leaning up to press their lips together briefly. "Just…for _once in your goddamn life_…shut up. Just stop talking and…let me, yeah?" He grinned breathlessly up at the older man, who could do nothing but gape stupidly at his friend's- let's not get into the topic of labels just yet, all right?- earnestness, nodding dumbly at Sam.

"Thanks," Sam smiled and kissed him again. He got to work on Gabriel's pants, unbuttoning and unzipping them deftly. Licking his lips anxiously, he pulled them and Gabriel's boxers down slightly. Just enough to liberate his cock, a little more than half-hard and begging for attention.

Once it was out in the open, Sam hesitated, trying to recall every single piece of advice and every tip he had read online. It looked like it was going to be a little more…difficult than Sam had previously thought. Gabriel was a lot bigger than anything he had practiced on.

Gabriel noticed Sam's nervousness and opened his mouth to say something reassuring and helpful and maybe slightly teasing, when Sam's tongue tentatively licked the underside of his dick and his words died with a full-body shudder. Sam tested out the taste on his tongue, and, deciding it wasn't completely awful, ducked down and suckled the mushroom head between his lips. It earned him a bit of a cry from Gabriel and, feeling satisfied and encouraged, he sunk down farther, sucking in another inch. Sam remembered not to suck in too much too fast, not to get to eager.

Sam continued sucking, being careful and precise, hand jacking off what he couldn't fit. He swirled his tongue around the shaft and pressed the tip into the slit and under the crown. He bobbed his head shallowly, slowly, and Gabriel was putty on the couch.

"F-Fuck, Sam," he was gasping, mumbling. "So good…_fuck_…_so _good. Mmmm…_too_ good…" There was an odd edge to Gabriel's voice at the end there and Sam looked up to see Gabriel watching him, brow furrowed. Sam popped off with a slick sound, frowning questioningly at him.

"Have you ever done this before?" Gabriel asked and maybe there was a flash of jealousy in his eyes and maybe it made Sam's stomach flip pleasantly.

"No," he replied with a smirk. "You're my first." Sam leaned up for one more chaste kiss before lowering himself back down and sucking the head back into his mouth, relishing the little moan it got out of the man above him.

"Jesus," Gabriel gasped. "Well then, you must be some kind of mutant freak natural-born cocksucker because _holy crap._" Sam felt equal parts irritated because, obviously, Gabriel couldn't even stop talking for _this _and equal parts smug that he was doing such a good job.

"Either that," Gabriel continued and Sam really wished he would _shut up _and just enjoy it, "or you Googled it."

Sam froze, lips stretched around the thick shaft, and looked up at Gabriel shyly through his lashes. Gabriel groaned and closed his eyes, holding up a hand to further block the view. "Jesus Christ, Sammich, don't just _look _at someone like that when their dick's in your mouth. _God. _I almost came."

Trying not to smirk around Gabriel's girth, Sam kept sucking, working as much as he could into his mouth. He was starting to get used to the musky, slightly salty taste and the warm, heavy weight. It wasn't bad, not at all. In fact, it was pretty nice and Sam found himself enjoying it despite the ache in his jaw.

"Of course you'd be the type to research this kind of stuff," Gabriel was saying and Sam resisted the urge to roll his eyes. "I bet you didn't even watch gay porn to jack off. You watched it to _study _them, didn't you? Giant friggin' nerd, you are." Sam felt warm, noting that Gabriel sounded fond, amused. Like he knew Sam so well and the fact that he would research giving a blowjob to be better at it was something endearing.

Sam moaned around Gabriel's dick and the vibrations got Gabriel to _finally _be quiet, falling back against the couch with a groan.

It was after a few more minutes of gentle sucking and licking that Sam's free hand snuck down past Gabriel's dick to fondle his balls and that was it.

"_Fuck, _Sam! I-I'm gonna…" He gave a sharp tug on Sam's hair and Sam took the hint, pulling off so just the head was in his mouth.

No matter how much he read and studied, nothing could prepare him for the feeling of someone coming into his mouth for the first time. The first spurt landed bitter on his tongue and Sam pulled off to swallow it down, the rest of it getting over Gabriel's dick and thighs, over Sam's fist wrapped around the shaft. As Gabriel whimpered and blinked blearily above him, Sam tested the aftertaste on his tongue. It wasn't _good_, per se. But it wasn't bad. He could get used to it.

Sam sat back on his heels and looked up at Gabe, head cocked like an interested puppy, little smirk playing on his lips. "Good?" he asked, curious despite himself.

"Not gonna lie, Sam," Gabriel replied, licking his lips and taking a deep breath. "Not the _best _head I've ever gotten…_but!" _he added hastily when Sam's 'kicked puppy' look started peeking through. "_But _it was great, and the best rookie head I've gotten. So just imagine how much better you'll be with a little practice." He waggled his eyebrows and Sam grinned brightly. Gabriel's eyes zeroed in on the corner of his lips and his smile slid off, eyes darkening. "You…you got a little…" He reached down and rubbed the corner of Sam's mouth with his thumb, cleaning off a drop of come. Moving on instinct, Sam surged forward, gripped Gabriel's wrist and sucked Gabriel's thumb clean, making the older man moan.

"Sweet fuck, you're going to be the death of me," he muttered. "Get up here, you giant girl. Gotta return the favor."

Excited at this new prospect, Sam jumped up and reclaimed his seat on the couch and Gabriel wasted no time in getting his lips on him. He gently lowered Sam, lying down next to him in the small amount of space available. His hand smoothed over Sam's chest as he licked into Sam's mouth.

Sam's hip twitched without Sam's consent and Gabriel pulled away to grin at him, Sam shrugging apologetically. "Someone's excited," Gabriel muttered.

"Shuddup, Gabe," Sam grumbled petulantly, making the older man chuckle.

"Don't worry, kiddo," the older man smirked at him. "I'll take care of you." And if that didn't reduce Sam to a loose, pliant, incoherently happy mess, nothing would.

As Gabriel kissed and sucked a mark onto Sam's neck, his hand trailed down Sam's chest to his pants, undoing them skillfully with one hand. He inched his hand inside Sam's boxers teasingly and Sam curled his fists to keep himself from reaching out and just shoving it all the way in.

After what felt like an eternity, Gabriel's hand finally curled around Sam's cock and pulled it out of his pants. There was a pause and Sam opened his eyes- and at what point had he closed them?- to look at Gabriel to see why he had stopped. Because, seriously, _why had he stopped?_

Gabriel was staring, mouth slightly agape, at Sam's dick in his hand. "Ho…ly…_shit, _Sammich," Gabriel murmured in reverence. "Puberty was _good _to you, wasn't it? You're friggin' _hung._"

"Ga_briel_," Sam groaned irritably, head falling back on the arm of the couch. It snapped Gabriel out of his dick-induced trance.

"Right, right, sorry. Just got hypnotized by your absolutely magnificent dick." Sam was about to reply, but Gabriel started jacking him off, and the less reason Gabriel had to talk and distract himself, the better for Sam.

It was slow and soft and Sam's hips rose slightly with every upstroke, his toes curling in his sneakers and his fingers digging into the threadbare fabric of Gabriel's thirdhand couch. He was biting a hole into his lips, little whimpers breaking through the back of his throat, Gabriel's lips on his neck driving him slowly insane.

Sam didn't last long, and he came with a gasp, little stars exploding behind his eyes, shooting all over Gabriel's hand.

"Hmm…see?" Gabriel said, all smug tones and cocky attitude. "Told you I'd take care of ya."

"Mmm," Sam hummed, too blissed out to give anything resembling a fuck, and Gabriel laughed softly.

"How coherent of you, brainiac." He kissed Sam's jaw and carefully crawled over him to slip of the couch, zipping himself back up in the process. "Stay here. I'll be right back, babe."

Sam's eyes shot open and his synapses reconnected. Gabriel just called him _babe._

Yeah, he could get used to that.

When Gabriel came back, he was carrying a wet washcloth and he used it to gently clean off Sam's dick before tucking him back in and washing both their hands. Sam hummed happily, soft smile on his lips.

"I shouldn't be surprised that you're the kind that gets sleepy after coming," Gabriel muttered fondly. "Come on." He tugged at Sam's hand. "Let's take this to the bed. You can nap and then we can go for round two or something."

As nice as a bed sounded, Sam didn't want to move. "No," he groused. "C'mere." He pulled Gabriel down and tucked him in against his chest. The couch was a little too small for them both because what Gabriel lacked in size, Sam made up for it. "Not goin' anywhere." There was a slight twang of the Kansas drawl that only came out when he was drunk or exhausted, and it made Gabriel smile.

"Apparently, you turn into a cowboy too." He shuffled like a content cat back against Sam's chest. "Good. I like cowboys."

Sam just grunted in response, arm squeezing Gabriel's waist briefly.

There was a silence where Gabriel thought Sam had nodded off, but then Sam said, "Hey, Gabe? I'm sorry about Kali…as much as I was hoping you two would break up already, I didn't mean for it to go about like this." For all of Sam's rancor towards Kali, he really didn't wish anything bad for her. He didn't have it in him to truly hate someone; he was too good a guy, and now it was weighing on his conscience.

Gabriel sighed. "I know, Sammich…I wish I could give her some better excuse, but, hell, what can I say? You're much more important to me."

If this ever got back to Dean, Sam would get the greatest hulking 'I told you so' slapped right in his face.

"Okay," Sam mumbled. "Love you, Gabe." Maybe they'd just gotten together a half hour or so ago…but he'd loved Gabriel since he was fourteen, so screw all established etiquette. He was going to tell him he loved him, dammit.

"Love you too, Samsquatch."

And maybe Sam's life was okay despite its many problems, just as long as each and every one of those dilemmas can somehow be traced back to, referred to, originated from, or be directly related to his best friend: Gabriel Novak.


End file.
